They're not exactly at the edge of a cliff, But they are divided by two different philosophies.
New York doesn't have any of the political connections in Chicago.
It's not that simple to move guys into another city 800 miles away and then expect them to start operating Bookmaking, Poker machines and Loan Sharking with no political connections. If that were the case, then anybody could go into Chicago and try and operate. It would never happen.
You cannot operate street rackets in a big city unless you have a lot of the Police and Politicians working with you.

When John DiFronzo, Pete DiFronzo, Joe Andriacchi & Marco D'Amico are all dead, maybe things will swing back the other way. Maybe a smaller newer Elmwood Park and Grand Ave Crew will make a comeback with brand new younger guys in the future and be partnered with Cicero. Who Knows?
I can tell you that the men's male and female relatives, mentioned above, will be running legitimate businesses and will use the connections of their deceased relatives to operate legitimately with maybe some white Collar crime attached to it. At that point, they won't be any different than some other smart well connected shrewd 'Legitimate' business people.